ArticleJournal of the American Chemical Society2016
Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
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- Exploring the Diverse Landscape of Fungal Cytochrome P450-Catalyzed Regio- and Stereoselective Dimerization of Diketopiperazines.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Molecular Dynamics Simulations Guide Chimeragenesis and Engineered Control of Chemoselectivity in Diketopiperazine Dimerases.Angewandte Chemie (International ed. in English) · 2023Article
- Total synthesis of complex 2,5-diketopiperazine alkaloids.The Alkaloids. Chemistry and biology · 2023Review
- Total Synthesis of the Proposed Structure of (-)-Novofumigatamide, Isomers Thereof, and Analogues. Part I.The Journal of organic chemistry · 2022Article
- Total Synthesis of (-)-Kopsifoline A and (+)-Kopsifoline E.Organic letters · 2021Article
- Structure and Function of NzeB, a Versatile C-C and C-N Bond-Forming Diketopiperazine Dimerase.Journal of the American Chemical Society · 2020Article
- Double the Chemistry, Double the Fun: Structural Diversity and Biological Activity of Marine-Derived Diketopiperazine Dimers.Marine drugs · 2019Review
- Phosphonate-Directed Catalytic Asymmetric Hydroboration: Delivery of Boron to the More Substituted Carbon, Leading to Chiral Tertiary Benzylic Boronic Esters.ACS catalysis · 2018Article
- Whole-genome sequencing of Aspergillus tubingensis G131 and overview of its secondary metabolism potential.BMC genomics · 2018Article
- Enantioselective Synthesis of Pyrroloindolines via Noncovalent Stabilization of Indole Radical Cations and Applications to the Synthesis of Alkaloid Natural Products.Journal of the American Chemical Society · 2018Article
- Concise total synthesis of (+)-asperazine A and (+)-pestalazine B.Organic & biomolecular chemistry · 2018Article
- Concise Synthesis of (-)-Hodgkinsine, (-)-Calycosidine, (-)-Hodgkinsine B, (-)-Quadrigemine C, and (-)-Psycholeine via Convergent and Directed Modular Assembly of Cyclotryptamines.Journal of the American Chemical Society · 2017Article
- Evaluation of Biosynthetic Pathway and Engineered Biosynthesis of Alkaloids.Molecules (Basel, Switzerland) · 2016Review
- Catalytic Carbocation Generation Enabled by the Mesolytic Cleavage of Alkoxyamine Radical Cations.Angewandte Chemie (International ed. in English) · 2016Article
- Convergent and Biomimetic Enantioselective Total Synthesis of (-)-Communesin F.Journal of the American Chemical Society · 2016Article
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3 authors.
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Abstract
The concise, enantioselective total syntheses of (+)-asperazine (1), (+)-iso-pestalazine A (2), and (+)-pestalazine A (3) have been achieved by the development of a late-stage C3-C8' Friedel-Crafts union of polycyclic diketopiperazines. Our modular strategy enables the union of complex polycyclic diketopiperazines in virtually their final forms, thus providing rapid and highly convergent assembly at the challenging quaternary stereocenter of these dimeric alkaloids. The significance of this carbon-carbon bond formation can be gauged by the manifold constraints that were efficiently overcome, namely the substantial steric crowding at both reactive sites, the nucleophilic addition of C8' over N1' to the C3 carbocation, and the multitude of reactivity posed by the use of complex diketopiperazine fragments in the coupling event. The success of the indoline π-nucleophile that evolved through our studies is notable given the paucity of competing reaction pathways observed in the presence of the highly reactive C3 carbocation generated. This first total synthesis of (+)-pestalazine A also allowed us to revise the molecular structure for this natural alkaloid.
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